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Milo’s Reference

A lot happened this week. My friend Raine Sillito who I met at my first AERO Conference three and a half years ago came down to visit Cloudhouse for the week, and joined us on a trip to Agile NYC.

We had a full week. During Milo and my co-working sessions, on the trains, and during a couple quiet moments at the beginning and end of days, I worked on a reference letter for Milo’s application to Buxton, the boarding school Milo want to go to next year. Will goes there now and loves it.

I don’t often interact with the traditional education world, outside of offering people red pills (to get out of the matrix). Finding myself writing Milo’s reference for the boarding school, I hit a wall, not because I didn’t want him to go. I want him to go because he wants to. I hit a wall because it felt really important to support him, and I felt all this pressure to articulate some of Milo’s beauty, growth, and gifts, knowing that doing so may affect him getting to do what he really wants. So I procrastinated, thought about it a bunch, thought about it more, procrastinated, wrote a little, thought more, talked to people about it, procrastinated, wrote more, edited a little, etc.

I ended up with this:


Reference for Milo


I have worked in Education for six years, and in that time I have have not met another young person (very few people of any age) with such a strikingly articulate self awareness coupled with such a mature and developed awareness of others. I have learned a lot from Milo.


This year Milo and I did Cloudhouse together. Last year I worked with Will Harris-Braun, and Milo, seeing what Will did with his freedom, wanted to do Cloudhouse. I did not have any other kids on board  for this year at that time and was prepared to pack up and work at another one of the Agile Learning Centers in my network, but Milo asked to do Cloudhouse, and because it clearly came from his heart, I committed to spending this year together.


Milo has a gift for facilitation. We’ve spent many, many hours this year, with a rotating pool of participants, playing MM. MM, or Magic and Monsters, is an oral tradition version of Dungeons and Dragons. Milo almost always DM’s (Dungeon Masters). Players create their characters in conversation with the DM who has the job of regulating their characters powers, qualities, and gear to maintain the integrity of the universe, while supporting players in expressing themselves in unique and novel ways. Once everyone has a character, the DM (Milo) creates a world, a set and setting, and populates it with non-player characters. Then the players explore and engage in the world, operating with free will, but beholdent to the laws of physics, magic, and the societies that the DM creates and upholds. Players can do anything, following as many motivations as in life, if not more for being unencumbered by the conventions and taboos of the real world. The DM manages the boundaries of the world, populates it, furnishes opportunities for stories and maintains them (because it gets boring without a good story), susses out the intentions and wishes of the players, and provides them with opportunities to achieve their goals, while constantly challenging them in battles, puzzles, intrigues, mysteries, politics, etc. Not everyone can DM well, it takes a lot of creativity, a lot of sensitivity, a lot of patience, a lot of persistence, a very good memory, a playful attitude, clear boundaries, and a willingness to change the world to make it more complex, interesting, and engaging. Milo has these qualities in and outside of the game. Milo’s gift for facilitating such games and groups has earned him recognition among the Agile Learning Community and in the intentional community we reside in.


A few months ago I hosted a retreat for twelve of the Agile Learning Facilitators from our four locations. On our last night together, after a long, intense three days of group work, we all needed some play. Milo came in and DM’d a game of Werewolves that we all still talk about as a high point of our year. This fourteen year old stood at the center of twelve educators and held the room, providing us with an opportunity to connect in a way that we all really needed. He absolutely shone, and since Milo had no obligations the next morning, and because of the flow, fun, and magic of the moment, I did not uphold a reasonable bedtime. Instead, I opted to throw reason out of the room, fed everyone dark chocolate, let Milo do his thing, and dove deeply into the joyous play of that wonderful night. The session concluded at four in the morning, with laughter, hugs, and twelve gifted, passionate educators in awe of Milo’s facility, candor, and focus.


I like Mark Twain’s adage: “the surest way to find out if you love or hate someone, is to travel with them. I have travelled with Milo and I love him. I want to honestly paint a picture of Milo, and of course, as a fourteen year old, or as any human, Milo’s not perfect. We went on a big road trip to the Agile Learning Center in NYC, the ALC in Charlotte, NC, Philedelphia, Virginia beach, and back to NYC for the People’s Climate March in the first month of Cloudhouse. In the midst of those foul teenage moments, characterized by low-blood sugar, inadequate sleep, teenage hormones, general grumpyness, feelings of being misunderstood, and any number of sundry concerns and awkwardnesses, Milo carries himself with a level of personal responsibility and strikingly articulate clarity, that I heretofore believed biologically impossible for a 15 year old. He has ups and downs like anyone, and carries no halo of immunity to the crap of the world, but I have no shame in acknowledging that his capacities in carrying himself amidst that crap without foisting on others, far exceed my own, and that I have grown in emotional maturity with Milo as a teacher.


This year we’ve made monthly trips to visit the Agile Learning Center in New York City. Milo has participated in planning, coordinating with hosts and his family, and navigating both the streets and transit systems of the city during these trips. On our last trip he led us confidently through multiple transit systems, and got his bearings as well as I could after a couple months of living in the city at nineteen. At home and at the other ALC’s, and when the facilitators and students from the other ALC’s have visited Cloudhouse, Milo has had a very fruitful impact as a solid role model, and I can say with absolute certainty that the other facilitators and students would wholeheartedly agree with this abbreviated representation of Milo, although they might shun me for the inadequacies and omissions.


Stepping up to responsibility, Milo took some time this year to space out. Just like Will last year, he spent a good deal of time not clear on what he wanted to do, and had trouble motivating himself to do some of the work he agreed to do as a homeschooler. This is a very common pattern for people entering into self directed learning environments. I see intrinsically motivated decisions to engage in productive struggle as a vital component to success in anything, school included, and it sometimes takes time for someone to discover their drive. I feel truly stoked to share with you that Milo has recently rounded that corner of motivation and how earnestly, and responsibly he shows up lately to do the work that gets him to where he wants to go. Milo wants to go to Buxton, and from what I have read and heard from parents and students he would have a lot to gain from going, and a lot to offer the community.



Eric Bear


Cloudhouse & Agile Learning Centers



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